Oxetane, 3,3-bis(chloromethyl)- → HCID 22247108, compound

HRID 1683431Notes

Reaction equation

HRID 1683431 reaction equation
Cl[CH2:2][C:3]1([CH2:7]Cl)[CH2:6][O:5][CH2:4]1.[F:9][C:10]([F:20])([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][OH:12].[H-].[Na+]>CN(C=O)C>[F:9][C:10]([F:20])([C:13]([F:18])([F:19])[C:14]([F:15])([F:16])[F:17])[CH2:11][O:12][CH2:2][C:3]1([CH2:7][O:12][CH2:11][C:10]([F:9])([F:20])[C:13]([F:18])([F:19])[C:14]([F:15])([F:17])[F:16])[CH2:6][O:5][CH2:4]1

Participants

5

Reactant 3

HCID 6550Oxetane, 3,3-bis(chloromethyl)-HCID 9776HeptafluorobutanolHCID 24758Sodium hydride

Product 1

HCID 22247108HCID 22247108, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to that described above, 3,3-bis(chloromethyl) oxetane (155 g, 1 mole) was reacted with 2,2,3,3,4,4,4-heptafluorobutan-1ol (402 g, 2.01 moles) in DMF (2 L) in the presence of sodium hydride (100 g of 50% dispersion in mineral oil, 2.3 moles) at 85° C. for 16 h to give 340 g (70%) of 3,3-bis(2,2,3,3,4,4,4-heptafluorobutoxymethyl) oxetane, a clear, colorless liquid. Glc analysis revealed the purity of this material to be in excess of 99%: BP=70°-72° C./1.0-1.3 mm-hG; 1H NMR (CDCl3) δ 4.44 (s, 4H), 3.97 (t, J=13.2 Hz), 3.86 (s, 4H); 13cNMR δ 43.9, 68.1 (t), 73.5, and 75.6 (Signals from carbons bearing fluorine are not included due to the complex splitting patterns and overlap of signals); 19fNMR δ -81.6 (3 F), -121.0 (2 F) and -128.3 (2 F); Anal. Calcd for C13H12F14O3 : C, 32.4; H, 2.5. Found: C, 32.3; H, 2.3.

Sources & evidence

ORD record
ord-80e1308a787b4f1492846947f5d2ea04
Source dataset
uspto-grants-1997_06
Patent number
US05637772

Reaction notes

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